The 20 Worst Cover Songs in Pop Music History

#16. "American Pie" - Madonna

Poor Madge. She started off with a groundbreaking spark, pushing both boundaries and buttons. But for the last decade, she seems more like that Molly Shannon character on SNL who can still high-kick in a leotard even though she's 60. Why a woman with an exclusively gay fan base would cover an allegory about classic rock history is beyond us; it's not like you can make a retro-dance remix that radio DJs will play in exchange for bribes from the record company that bought your soul.

#15. "My Generation" - Hilary Duff

030707/15HilaryDuff_MyGeneration.mp3

People try to put your generation down, do they, Hilary? Maybe it's because your generation has a habit of mistaking glorified Mouseketeers for musicians. Or maybe it's because your generation gave rise to a version of the music industry that asparagus-pisses in the face of everything rock stands for. Either way, it looks like Hilary's in the process of following her own advice and just f-f-f-fading away.

#14. "It's My Life" - No Doubt

No Doubt's note-for-note recreation of this song by Talk Talk isn't excruciating, in the same way that having to make small talk with Gwen Stefani for ten minutes would be, but you have to ask: why do it in the first place? So that you can act in an incoherent video that has nothing to do with the song? Because you've already done that at least five times by now. If you're still practicing, stop: you've got the chops.

#13. "Video Killed The Radio Star" - The Presidents of the United States of America

With so many brilliant tunes out there to cover, why would you pick The Buggles' goofy hit from 1980? Were the Presidents seduced by the questionably hot chicks in the headbands and legwarmers? Was it the timely nature of the lyrics, which had become completely irrelevant by 1998? Or, most likely, did the POTUS just assume you could drench anything in wink-nudge irony and the kids'd lap it up like bong resin? Regardless, adapting this '80s classic to fit the late '90s is like adapting the patent for the first automobile into a screenplay for a romantic comedy: the only way it'd sound like a good idea is if you were high or stupid. So what I'm saying is it makes sense they'd give it a shot.